p-Toluenesulfonic acid → HCID 12150670, compound

Participants

Reaction Steps

A mixture of p-toluenesulfonic acid (163 mg, 0.86 mmol) and 2-({4-[3-(Cyclobutyl-methyl-carbamoyl)-4-hydroxy-phenoxy]-3,5-dimethyl-phenyl}-hydrazono)-propionic acid ethyl ester (259 mg, 0.57 mmol) in toluene (2 mL) was heated to reflux. After vigorously stirring at reflux for 1 hour, the reaction mixture was then allowed to cool to room temperature. To which was added saturated aqueous NaHCO3 (15 mL) and EtOAc (20 mL). The EtOAc layer was separated, washed with saturated NaHCO3 (2 times 25 mL), brine (25 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by preparative TLC (4% MeOH in CH2Cl2) to afford the title compound (136 mg) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ9.45 (s, 1H), 8.89 (br s, 1H), 7.23 (s, 1H), 7.16 (s, 1H), 7.04 (dd, 1H), 6.97 (d, 1H), 6.42 (d, 1H), 4.46-4.38 (m, 3H), 2.93 (s, 3H), 2.36 (s, 3H), 2.26 (s, 3H), 2.22-2.01 (m, 2H), 1.74-1.54 (m, 2H), 1.43 (t, 3H), 1.36-1.20 (m, 2H). MS (APCI+) Calc: 436.2, Found: 437.3 (M+1).

Provenance & Evidence